RSS-Feed abonnieren
DOI: 10.1055/s-0030-1258236
Cerium(III)-Catalyzed Facile Synthesis of Dihydrobenzofuran-Tethered Pyridines and Dihydroquinolin-5(6H)-ones from β-Enaminones
Publikationsverlauf
Publikationsdatum:
30. August 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201021/lookinside/thumbnails/10.1055-s-0030-1258236-1.jpg)
Abstract
A series of novel dihydrobenzofuran-tethered pyridines, dihydroquinolin-5(6H)-ones, and indeno[1,2-b]pyridin-5-ones were synthesized in very good yields by CeCl3˙7H2O-NaI catalyzed one-pot condensation of variants of the Bohlmann-Rahtz reaction, viz. β-enaminones derived from 7-acetyldihydrobenzofurans, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. The protocol offers the advantages of easily accessible substrates, shorter reaction times, and easy work-up with a readily available catalyst. Further more, dihydrobenzofuran-substituted 2-(chloromethyl)pyridine was derivatized to its synthetic hybrid by reacting with piperazine.
Key words
Bohlmann-Rahtz reaction - dihydrobenzofuran - CeCl3˙7H2O-NaI - one-pot condensation - β-enaminone - heterocycles - pyridines - quinolinones
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Spandl RJ.Bender A.Spring DR. Org. Biomol. Chem. 2008, 6: 1149 -
1b
Tan DS. Nat. Chem. Biol. 2005, 1: 74 -
1c
Bagley MC.Dale JW.Merritt EA.Xiong X. Chem. Rev. 2005, 105: 685 -
1d
Burke MD.Schreiber SL. Angew. Chem. Int. Ed. 2004, 43: 46 -
1e
Henry GD. Tetrahedron 2004, 60: 6043 -
2a
Aulakh VS.Ciufolini MA. J. Org. Chem. 2009, 74: 5750 -
2b
Bagley MC.Chapaneri K.Dale JW.Xiong X.Bower J. J. Org. Chem. 2005, 70: 1389 -
2c
Bagley MC.Xiong X. Org. Lett. 2004, 6: 3401 -
2d
Bagley MC.Dale JW.Xiong X.Bower J. Org. Lett. 2003, 5: 4421 -
2e
Bagley MC.Dale JW.Ohnesorge M.Xiong X.Bower J. J. Comb. Chem. 2003, 5: 41 -
2f
Bagley MC.Bashford KE.Hesketh CL.Moody CJ. J. Am. Chem. Soc. 2000, 122: 3301 - For streptonigrin:
-
3a
Harding MM.Long GV.Brown CL. J. Med. Chem. 1993, 36: 3056 - For cerivastatin:
-
3b
Angerbauer R.Bischoff H.Steinke W.Ritter W. Drugs Future 1994, 19: 537 -
3c
Chen B.-C.Bednarz MS.Zhang H.Guo P.Jemal M.Robl JA.Biller SA.Sundeen JE.Balasubramanian B.Barrish JC.
J. Labelled Compd. Radiopharm. 2006, 49: 311 - For lavendamycin:
-
3d
Hassani M.Cai W.Holley DC.Lineswala JP.Maharjan BR.Ebrahimian GR.Seradj H.Stocksdale MG.Mohammadi F.Marvin CC.Gerdes JM.Beall HD.Behforouz M. J. Med. Chem. 2005, 48: 7733 - 4 For a review of the chemistry and
synthesis of benzofurans, see:
Hou X.-L.Yang Z.Wong HNC. Furans and Benzofurans, In Progress in Heterocyclic Chemistry Vol. 14:Gribble GW.Gilchrist TL. Pergamon; Oxford: 2002. p.139-179 -
5a
Lu B.Wang B.Zhang Y.Ma D. J. Org. Chem. 2007, 72: 5337 -
5b
Hagihara K.Kashima H.Iida K.Enokizono J.Uchida S.-i.Nonaka H.Kurokawa M.Shimada J. Bioorg. Med. Chem. Lett. 2007, 17: 1616 -
5c
Dixit M.Sharon A.Maulik PR.Goel A. Synlett 2006, 1497 -
5d
Wyatt PG.Allen MJ.Chilcott J.Gardner CJ.Livermore DG.Mordaunt JE.Nerozzi F.Patel M.Perren MJ.Weingarten GG.Shabbir S.Woollard PM.Zhou P. Bioorg. Med. Chem. Lett. 2002, 12: 1405 - For recent reviews and books see:
-
6a
Sunderhaus JD.Martin SF. Chem. Eur. J. 2009, 15: 1300 -
6b
Ramon DJ.Yus M. Angew. Chem. Int. Ed. 2005, 44: 1602 -
6c
Domling A. Chem. Rev. 2006, 106: 17 -
6d
Multicomponent
Reactions
Zhu J.Bienaymé H. Wiley; Weinheim: 2005. -
6e
Ramon DJ.Yus M. Angew. Chem. Int. Ed. 2005, 44: 1602 -
6f
Banfi L.Riva R. Org. React. 2005, 65: 1 -
6g
Hulme C.Gore V. Curr. Med. Chem. 2003, 10: 51 -
7a
Ganem B. Acc. Chem. Res. 2009, 42: 463 -
7b
Zhu W.Mena M.Jnoff E.Pasau P.Ghosez L. Angew. Chem. Int. Ed. 2009, 48: 5880 -
7c
Elders N.van der Born D.Hendrickx LJD.Timmer BJJ.Krause A.Janssen E.de Kanter FJJ.Ruijter E.Orru RVA. Angew. Chem. Int. Ed. 2009, 48: 5856 -
8a
Bagley MC.Glover G.Merritt EA. Synlett 2007, 2459 -
8b
Merritt EA.Bagley MC. Synlett 2007, 954 -
8c
Bohlmann F.Rahtz D. Chem. Ber. 1957, 90: 2265 -
9a
Kantevari S.Chary MV.Vuppalapati SVN. Tetrahedron 2007, 63: 13024 -
9b
Kantevari S.Chary MV.Vuppalapati SVN.Lingaiah N. J. Heterocycl. Chem. 2008, 1009 -
10a
Wan J.-P.Pan Y.-J. Chem. Commun. 2009, 2768 -
10b
Alnajjar A.Abdelkhalik MM.Al-Enezi A.Elnagdi MH. Molecules 2009, 14: 68 -
10c
Riyadh SM.Abdelhamid IA.Al-Matar HM.Hilmy NM.Elnagdi MH. Heterocycles 2008, 75: 1849 -
10d
Lieby-Muller F.Allais C.Constantieux T.Rodriguez J. Chem. Commun. 2008, 4207 -
10e
Senaiar RS.Young DD.Deiters A. Chem. Commun. 2006, 1313 -
10f
Davis JM.Truong A.Hamilton AD. Org. Lett. 2005, 7: 5405 -
10g
Bashford KE.Burton MB.Cameron S.Cooper AL.Hogg RD.Kane PD.MacManus DA.Matrunola CA.Moody CJ.Robertson AAB.Warne MR. Tetrahedron Lett. 2003, 44: 1627 -
10h
Al-Saleh B.Abdelkhalik MM.Eltoukhy AM.Elnagdi MH. J. Heterocycl. Chem. 2002, 39: 1035 -
10i
Omran FA.Awadi NA.Khair AAE.Elnagdi MH. Org. Prep. Proced. Int. 1997, 29: 285 -
11a
Tambade PJ.Patil YP.Bhanage BM. Curr. Org. Chem. 2009, 13: 1805 -
11b
Comelles J.Moreno-Mañas M.Vallribera A. ARKIVOC 2005, ix: 207 ; http://www.arkat-usa.org/home -
12a
Bartoli G.Marcantoni E.Sambri L. Synlett 2003, 2101 -
12b
Bartoli G.Fernández-Bolaños JG.Antonio GD.Foglia G.Giuli S.Gunnella R.Mancinelli M.Marcantoni E.Paoletti M. J. Org. Chem. 2007, 72: 6029 -
12c
Khodaei MH.Khosropour AR.Kookhazadeh M. Synlett 2004, 1980 -
12d
Christofeers J.Kauf T.Werner T.Rossle M. Eur. J. Org. Chem. 2006, 2601 -
12e
Sabitha G.Reddy GSKK.Reddy KB.Reddy NM.Yadav JS. Adv. Synth. Catal. 2004, 346: 921 -
12f
Sabitha G.Babu RS.Rajkumar M.Srividya R.Yadav JS. Org. Lett. 2002, 4: 343 - 13
Huang Z.Zhao Q.Huang R.Wang Q. Lett. Org. Chem. 2009, 6: 29
References
CCDC-771475 (3aa) and CCDC-771476 (3ae) contain the crystallographic data and can be obtained free of charge from the Cambridge Crystallographic Data centre via www.ccdc.cam.ac.uk/data_request/cif.